Tuscany is a renowned destination for a reason. With its rolling hills, picturesque vineyards, and medieval towns, this region of central Italy has something for everyone. But what makes the region is unique are its best towns to visit in Tuscany.
That’s right – Tuscany is the perfect place to slow down, relax, and enjoy the good life.
Here we will discuss 15 of the prettiest towns in Tuscany, Italy. We will also discuss how many days you need to say in Tuscany and how you can get there.
Let’s get started, you’ll love these villages in Tuscany.
15 Best Towns to Visit in Tuscany
Tuscany is known for its picturesque hills, medieval villages, and vineyards. While there are many towns and villages worth visiting, here are 15 of the most beautiful, small towns in Tuscany.
San Gimignano
San Gimignano is a small town in Tuscany, Italy, about an hour’s drive from Florence. This town is best known for its many medieval towers and excellent white wines.
Its charming medieval streets are lined with colorful houses, and its hilltop location offers stunning views of the surrounding countryside. San Gimignano is also home to a number of historical monuments, including the imposing Gothic cathedral, the Palazzo del Popolo, and a stunning, calm main square.
Visitors to San Gimignano can enjoy exploring its many shops and restaurants or simply take in its picturesque setting.
With its rich history and beautiful scenery, San Gimignano is an ideal destination for travelers looking to experience the best of what Italy has to offer.
Activities in San Gimignano
- Piazza del Duomo
- Palazzo del Popolo
- Tower and Casa Campatelli
- Piazza della Cisterna and its Towers
- San Gimignano Museum of Torture
Pienza
The Tuscan town of Pienza is located approximately 80 miles southeast of Florence and is best known for its Renaissance-era architecture, which Pope Pius II commissioned in the 15th century.
Today, much of the town’s original architecture remains well-preserved, making it a popular tourist destination. In addition to its architectural significance, Pienza is also home to several historical landmarks, including the Palazzo Piccolomini and the Duomo di Pienza.
The historic town proximity to other Tuscan towns, such as Montepulciano and Cortona, makes it an ideal base for exploring the Val d’Orcia. Last but not least, you’ll love the panoramic terrace and the views over the Tuscan countryside!
Activities in Pienza
- Piazza Pio II
- Pienza Cathedral
- Bishop’s Palace
- Palazzo Piccolomini and its Gardens
- See the views from the Panoramic Terrace
Siena
Siena is another of the best towns in Tuscany that you can’t leave without visiting. It’s only a one-hour drive away from Florence, which is definitely a plus.
Known for its medieval brick buildings and imposing cathedral, you can roam around and discover Piazza del Campo as well as Palazzo Pubblico, the town hall.
It’s worth noting that the Siena historic center is a UNESCO World Heritage Site, and it’s easy to see why it’s one of the most beautiful Tuscan towns to visit.
Siena Cathedral has a gothic design with black-and-white stripes, while the Duomo contains art by Pisano, Michelangelo, and Bernini. Most visitors come to see Siena’s Duomo (cathedral) and associated museums or to visit the historic palaces scattered throughout the medieval city center.
On top of that, every summer, the streets of Siena fill with the sound of pounding hooves as competitors come to compete in the Palio of Siena.
The districts compete in trials for ten days leading up to the race to determine which horse and rider will represent them in the Palio. On race day, the riders line up in front of Siena’s magnificent cathedral and prepare to enter the city’s ancient main square.
Can you think of a more authentic experience in Tuscany?
With abundant museums, art galleries, piazze, palaces, and churches, Siena rivals Florence and is definitely one of the best Tuscan towns I really urge you to visit.
Activities in Siena
- Fonte Gaia
- Duomo di Siena
- See the Palio of Siena
- Battistero di San Giovanni
- Piazza del Campo and Palazzo Pubblico
Lucca
Lucca is one of the most famous towns of Tuscany to visit if you’re looking for a taste of medieval Italy. This picturesque town is home to a well-preserved wall that dates back to the 16th century.
The wall, which measures over 4 kilometers, is ideal for a leisurely stroll or bike ride. Once you’ve worked up an appetite, sample some of the local cuisine, including dishes such as ribollita (a hearty soup made with beans and vegetables) and Panzanella (a bread and tomato salad).
And of course, no visit to Lucca would be complete without enjoying a glass or two of the local Chianti on a wine tasting session.
So whether you’re looking to explore Italy’s rich history or relax in a beautiful setting, the town of Lucca is sure to exceed your expectations.
Activities in Lucca
- Guinigi Tower
- Lucca Cathedral
- Piazza dell’Anfiteatro
- Ponte della Maddalena
- Walk Around the Town Walls
- Church of San Michele in Foro
- National Museum of Villa Guinigi
Volterra
Volterra is a beautiful Tuscan hill town in southwestern Tuscany, about an hour’s drive from Florence and Siena. This town is best known for its many art galleries, museums, and beautifully preserved medieval architecture.
The town is home to a number of historical landmarks, including the Roman Theater, the Palazzo dei Priori, and the Cathedral. There are also several museums in Volterra, including the Etruscan Museum and the Archaeological Museum.
In addition, visitors can enjoy the town’s many shops and restaurants or take a day trip to one of the nearby towns or villages.
All in all, Volterra is one of Tuscany’s most beautiful places to visit, and you’ll quickly understand as you as get there.
Activities in Volterra
- Roman Theater
- Etruscan Museum
- Palazzo dei Priori
- Volterra Cathedral
- Baptistery and Diocesan Museum
Monteriggioni
Next is Monteriggioni, a tiny, remote town located 20km north of Siena, or about 25 minutes by car, and one of the most beautiful villages in Tuscany.
It is best known for its well-preserved medieval walls dating back to the 12th century. The walls feature 14 towers, and visitors can walk along the top of the walls for panoramic views of the town and the surrounding countryside.
The historic city is also home to several museums, churches, and other historical sites. In addition, the town is located just minutes from some of Tuscany’s most popular wineries.
As a result, Monteriggioni is the perfect place to relax and have a short break before continuing your trip around the Tuscan countryside.
Activities in Monteriggioni
- Piazza Roma
- Museum of Arms
- Church of Santa Maria Assunta
- Have Lunch at Osteria Antico Travaglio
- Walk on the City wall and its 14 Towers
Montepulciano
Montepulciano is another hilltop town in southeastern Tuscany, about an hour’s drive from Siena. This town is best known for its many vineyards, wineries, and stunning Renaissance-era architecture.
Nestled in the Val d’Orcia, this medieval town has a beautiful bell tower and it is quite picturesque.
There are several wineries in Montepulciano that offer tours and tastings, making it the perfect destination for wine lovers. In addition, the town is home to a number of traditional restaurants, serving classic Tuscan dishes such as Florentine steak and chicken liver pate.
And when here, don’t forget to taste the local lovely wine, the Vino Nobile di Montepulciano.
Activities in Montepulciano
- Piazza Grande
- Palazzo Avignonesi
- Church of San Biagio
- Have a drink at Caffè Poliziano
- Church of Santa Maria dei Servi
Cortona
This town is full of culture and history, with beautiful architecture and views everywhere you turn.
If you are looking for a travel destination that is rich in history and culture, then Cortona is the perfect place for you. Cortona is a small town in southern Tuscany, about midway between Florence and Rome, and it has long been a popular tourist destination.
You can also explore the lovely alleys, visit the Etruscan Academy Museum, which houses a collection of artefacts from the Etruscan civilization, and see the Convento delle Celle.
In addition, Cortona is known for its abundance of idyllic landscapes, making it the perfect place to enjoy a leisurely stroll or a picnic lunch.
Activities in Cortona
- Convento delle Celle
- Etruscan Archaeology Museum
- Santa Margherita
- Piazza della Repubblica
- Diocesan Museum
Suvereto
If you’re after a laid-back town in Tuscany that offers sensational views while being located close to the beach, then Suvereto is your best bet.
Suvereto is a small town located in the province of Livorno in Tuscany, Italy. The town is situated on a hill in an area of outstanding natural beauty. It is surrounded by forests, vineyards, and olive groves and has stunning views of the Mediterranean Sea.
Suvereto has a long history, dating back to Roman times. Today, it is a popular tourist destination, with many visitors enjoying the town’s relaxed atmosphere and excellent food and wine.
There are several delicious restaurants in Suvereto and some interesting shops and galleries. The town is well worth a visit if you want to taste the real Tuscan lifestyle.
Activities in Suvereto
- Convent of San Francesco
- Church of San Giusto Vescovo
- Rocca Aldobrandesca of Suvereto and Its Museum
Pitigliano
Pitigliano is nestled in southern Tuscany, in the province of Grosseto, and is one of Central Italy’s hidden gems. Its history dates back to Etruscan times, and it was once an important center of trade. Nowadays, Pitigliano is best known for its beautiful architecture and stunning setting.
The town is built on a tufa cliff, and its streets are lined with medieval houses. Visitors can explore the town’s many churches and museums or take a walk through its cobbled streets.
Pitigliano is also home to several wineries, making it the perfect place to relax and enjoy some of Italy’s finest wines.
Whether you’re looking for history, culture, or just a beautiful place to relax, Pitigliano should be on your list of places to visit.
Activities in Pitigliano
- Orsini Palace
- Cathedral of Pitigliano
- Piazza della Repubblica
- Fontana delle Sette Cannelle Fountain
Arezzo
Arezzo is one of the best towns in Tuscany for visitors who want to experience the true flavor of the region. Located in central Italy, Arezzo is home to a number of well-preserved Renaissance monuments, as well as a vibrant art and culture scene.
The town is also surrounded by picturesque rolling hills and vineyards, making it the perfect base for exploring the Tuscan countryside. Visitors can enjoy strolling through Arezzo’s winding streets, sampling the local cuisine, and browsing the shops for handmade Ceramics and leather goods.
With its lovely setting and wealth of things to see and do, it’s no wonder that Arezzo is one of the most popular destinations in Tuscany.
Activities in Arezzo
- Piazza Grande
- Duomo San Donato
- Parco Sandro Pertini
- Archaeological Museum of Arezzo
- Church of Santa Maria della Pieve
Anghiari
While visiting Arezzo, if you want to discover the most original and best town in Tuscany, Anghiari is a safe option. In fact, it is a raw, untouched village that will transport you back in time as soon as you get here.
The town is situated on a hilltop and offers stunning views of the nearby valleys and mountains. Anghiari is home to several historic buildings and artwork, making it an ideal destination for those interested in history and culture.
The town also offers a variety of shops and restaurants, despite its small size, as well as an outdoor market where you can purchase local produce and handicrafts.
With its beautiful setting and stunning views from above, Anghiari is one of the best towns in Tuscany to visit.
Activities in Anghiari
- Museum of the Battles
- Church of Santo Stefano
- Museum of Palazzo Taglieschi
- Chuch of Santa Maria delle Grazie
- Have a Meal at Cantina Del Granduca
Castelnuovo di Garfagnana
Tuscany is one of the most beautiful regions in all of Italy. With its rolling hills, medieval towns, and stunning views, it’s no wonder that so many people flock here each year. And while countless towns are worth exploring, Castelnuovo di Garfagnana is definitely one of the best.
Nestled in the Garfagnana Valley in the Lucca province, this town is surrounded by forests and mountains. There’s plenty to see and do here, from hiking and biking to exploring the historic center.
But what makes Castelnuovo di Garfagnana special is its sense of community. The locals are warm and welcoming and take pride in their town’s history and culture. If you’re looking for a true taste of Tuscany, Castelnuovo di Garfagnana is the perfect place to start.
Activities in Castelnuovo di Garfagnana
- Rocca Ariostesca
- Teatro Alfieri Theater
- Fortress of Mont’Alfonso
- Hike Up to One of the Trails
Montalcino
There’s something magical about the Tuscan hills, and the town of Montalcino is a perfect example. Perched on a hilltop, surrounded by vineyards and olive groves, Montalcino is one of the beautiful hill towns you can’t miss.
The views are simply incredible, and there’s plenty to explore, from the medieval fortress to the quaint cobbled streets. But what really makes Montalcino special is its wine.
Some of the best Brunello di Montalcino wines come from this town, and there are plenty of wineries to visit (not to mention plenty of opportunities to taste the delicious local wine!).
If you’re looking for a town that oozes charm and charisma, Montalcino is the perfect place to visit.
Activities in Montalcino
- Palazzo dei Priori
- Fortress of Montalcino
- Cathedral of the Holy Savior
- Church of Our Lady of Soccour
- Belvedere di Montalcino Viewpoint
- Have Lunch at Taverna del Grappolo Blu
Pontedera
If you’re looking for the best towns in Tuscany to visit, Pontedera should be at the top of your list. Situated only 30km from Pisa, this charming town is located in the heart of Tuscany, and it’s the perfect destination for a day trip in Tuscany.
Explore the town’s medieval streets and visit its famous churches and museums when you’re here. If you’re a fan of Tuscan wine, you’ll also want to tour one of the many wineries in the area.
And, of course, no trip to Pontedera would be complete without enjoying a delicious meal at ArteGrill, one of the best places to eat around.
Of course, visiting the leaning tower of Pisa is a must, but I highly recommend you come visit Pontedera once you’re done with your visit.
Activities in Pontedera
- Piaggio Museum
- Misericordia Church
- Misericordia Church
- Parrocchia del Sacro Cuore
- Walk Around the City and Via I° Maggio
Best Towns in Tuscany – FAQ
Best Months to Visit Tuscany
The best time to visit Tuscany is during the spring or fall months. April and May are some of the most beautiful times to visit when temperatures are mild, and there are fewer crowds. The summer can be quite hot, though it’s a great time to swim in the sea. Additionally, September and October offer beautiful colors as the trees begin to change.
How Many Days do You Need in Tuscany?
The best way to experience Tuscany is to take your time and explore the region. We recommend at least 7-10 days to appreciate the area’s beauty and culture.
How to Get Around in Tuscany?
The easiest way to get around Tuscany is by car. You can rent a car in Italy and drive around Tuscany, which makes your day trips around much more convenient.
What is the Best Town in Tuscany?
Out of all towns in Tuscany, San Gimignano is widely considered to be the best. Set atop a hill, San Gimignano offers breathtaking views of the surrounding Tuscan countryside.
This charming medieval town is full of art and architecture from the 13th and 14th centuries, including towers built by wealthy families as status symbols.
There are dozens of churches, and some even contain frescoes from the Renaissance period. The most iconic sight in San Gimignano is its skyline, which consists of fourteen towers that stand majestically against the sky.
What is the Most Beautiful Area of Tuscany?
One of the most famous and picturesque areas of Tuscany is the Val d’Orcia, located in the southern part of the region. The rolling hills, olive groves, and vineyards of this area have inspired artists and poets for centuries.
The town of Pienza, a UNESCO World Heritage Site, is located in the heart of Val d’Orcia and is known for its Renaissance architecture and beautiful views of the surrounding countryside.
Another popular area is the Chianti region, located between Florence and Siena. This area is known for its beautiful vineyards, charming hilltop towns, and stunning views of the Tuscan countryside.
What is the Best Part of Tuscany?
Tuscany is a beautiful region in central Italy, known for its stunning countryside, rich history, and delicious food and wine. There are many wonderful places to visit in Tuscany, each with their own unique charms, but some of the best parts of Tuscany include:
- Florence: Florence is the capital city of Tuscany and one of the most beautiful cities in Italy. It’s known for its stunning architecture, world-class art museums, and delicious food.
- Chianti: Chianti is a wine region located between Florence and Siena. It’s famous for its red wines, rolling hills, and charming medieval villages.
- Val d’Orcia: Val d’Orcia is a stunning valley in southern Tuscany that’s known for its beautiful landscapes, picturesque towns, and delicious food.
- Siena: A charming medieval town in central Tuscany famous for its beautiful cathedral, stunning main square, and unique horse race called the Palio.
- Lucca: Lucca is a beautiful walled city located in northern Tuscany. It’s known for its charming narrow streets, beautiful piazzas, and delicious food.
What Town is the Heart of Tuscany?
While there are many beautiful and historic towns in Tuscany, Florence is often considered the heart of Tuscany. As the regional capital, Florence is the cultural and artistic center of the region, and it played a crucial role in the development of the Renaissance.
Florence is home to many famous works of art and architecture, including the Duomo, the Uffizi Gallery, and Michelangelo’s David, and it’s also known for its delicious food and wine.
However, other towns such as Siena, Pisa, Lucca, San Gimignano, and Arezzo are also considered important and represent the heart of Tuscany in their own way.
Which is Better – Siena or Lucca?
Both Siena and Lucca are beautiful and charming towns in Tuscany, but they offer very different experiences.
Siena is a hilltop medieval city known for its stunning cathedral, medieval architecture, and unique horse race called the Palio. Siena’s historic center is pedestrian-friendly and full of narrow, winding streets and beautiful piazzas. The city also has many art museums and galleries, as well as delicious food and wine.
On the other hand, Lucca is a walled city known for its well-preserved Renaissance-era walls, cobblestone streets, and charming piazzas. Lucca is also famous for its music scene, with famous musicians such as Puccini. The city is also a great place for biking, with a network of bike paths that follow the top of the city walls.
Choosing between Siena and Lucca really depends on what you’re interested in. If you’re interested in history, architecture, and art, Siena may be a better choice. Lucca may be the better choice if you’re more interested in Renaissance-era architecture, biking, and music.
Where is the Best Place to Stay in Tuscany?
Florence is the best place to stay in Tuscany because of its convenient location and endless attractions. It boasts numerous historical sites, museums, churches and monuments, making it the perfect base for day trips to nearby towns such as Pisa.
Also, car rentals are easy to come by in Florence, making it easy to explore more of Tuscany’s breathtaking landscapes.
With Florence as your home base, you can easily access some of Italy’s most renowned cultural destinations while still having plenty of time to relax and marvel at the beauty of the Tuscan countryside.
More Italy Travel Guides
- Pisa Tour from Florence – Travel Guide
- 10 Best Day Trips from Florence, Italy
- Plan the Perfect 3-day Itinerary in Florence
- This is the Best Time to Visit Matera
- How Much Does a Trip to Italy Cost?
- Unique Places to Travel in Europe – Italy
Conclusion
There you have it – 15 of the most beautiful towns to visit in Tuscany. Whether you’re looking for culture and history, delicious food and wine, or stunning views, there’s something for everyone in this part of Italy.
From the UNESCO World Heritage Site of Siena to San Gimignano and Cortona, these were the most beautiful towns in Tuscany, Italy.
So make sure to add these destinations to your trip to Italy, you definitely won’t regret it.
